1-Pyrenylboronic acid Chemical Properties

Melting point:

247-251 °C(lit.)

Boiling point:

509.4±33.0 °C(Predicted)

Density 

1.35±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

pka

8.53±0.30(Predicted)

form 

Powder

color 

Pale yellow

Water Solubility 

Slightly soluble in water.

InChI

InChI=1S/C16H11BO2/c18-17(19)14-9-7-12-5-4-10-2-1-3-11-6-8-13(14)16(12)15(10)11/h1-9,18-19H

InChIKey

MWEKPLLMFXIZOC-UHFFFAOYSA-N

SMILES

B(C1=C2C3=C4C(C=C2)=CC=CC4=CC=C3C=C1)(O)O

CAS DataBase Reference

164461-18-1(CAS DataBase Reference)

Safety Information

Safety Statements 

24/25

WGK Germany 

3

HS Code 

29319090

MSDS

• Language:English Provider:SigmaAldrich

1-Pyrenylboronic acid Usage And Synthesis

Chemical Properties

White to light brown solid

Uses

It is an important raw material and intermediate used in organic synthesis agrochemical, pharmaceutical and dyestuff field. Also used as a intermediate for organic light-emitting diode(OLED).

Uses

suzuki reaction

Synthesis

The general procedure for the synthesis of 1-pyrenylboronic acid from trimethyl borate and 1-bromopyrene was as follows: 1-bromopyrene (30 g, 107 mmol) was added to a round-bottom flask and dissolved in 240 mL of tetrahydrofuran (THF). Under cooling conditions, n-BuLi (1.6 M, 80 mL) in hexane was slowly added dropwise, keeping the reaction temperature at -78 °C. After the dropwise addition was completed, the reaction mixture continued to be stirred at -78 °C for about 1 hour. Subsequently, trimethyl borate (15.5 g, 149 mmol) was added and stirring was continued at -78 °C for 1 hour. After that, the reaction mixture was warmed up to room temperature and stirred for about 2 hours. After completion of the reaction, the reaction solution was adjusted to acidic with 2N HCl. Extraction was carried out with ethyl acetate (EA) and hexane, and the organic phases were combined and concentrated under reduced pressure to remove the solvent to give 19.5 g of 1-pyrenylboronic acid in 74% yield.

References

[1] Patent: KR101515814, 2015, B1. Location in patent: Paragraph 0343; 0344
[2] Patent: KR101503771, 2015, B1. Location in patent: Paragraph 0215; 0216
[3] Patent: US2014/131664, 2014, A1. Location in patent: Paragraph 0025-0026
[4] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1998, # 7, p. 1263 - 1268
[5] ChemPlusChem, 2013, vol. 78, # 10, p. 1288 - 1295

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